Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines

被引：121

作者：

Capek, Petr ^{[1
]}

Pohl, Radek ^{[1
]}

Hocek, Michal ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Ctr New Antivirals & Antineoplast, CZ-16610 Prague 6, Czech Republic

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 11期

关键词：

D O I：

10.1039/b604010a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expeditious and highly efficient single-step methodology for the introduction of a phenylalanine moiety into position 8 and 6 of the purine scaffold was developed based on aqueous-phase Pd-catalysed Suzuki - Miyaura cross-coupling reactions of unprotected 4-boronophenylalanine with 8-bromo- or 6-chloropurines. The scope of the methodology was demonstrated by syntheses of unprotected (adenin-8-yl) phenylalanine base, nucleosides, nucleotides and nucleoside triphosphates as well as (purin-6-yl) phenylalanine base and nucleosides. All these products were obtained in high yields and in optically pure form.

引用

页码：2278 / 2284

页数：7

共 42 条

[1]

Amann N, 2002, SYNLETT, P687

[2] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].